Trityl chloride → HCID 66592352, compound

HRID 1994346Notes

Reaction equation

HRID 1994346 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:21][CH2:22][C:23]1[CH2:28][C:27](=[O:29])[C:26]([O:30][CH3:31])=[CH:25][N:24]=1>CN(C)C1C=CN=CC=1.CN(C)C=O.O>[CH3:31][O:30][C:26]1[C:27](=[O:29])[CH2:28][C:23]([CH2:22][O:21][C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:24][CH:25]=1

Participants

6

Reactant 2

HCID 6456Trityl chlorideHCID 66591964HCID 66591964, compound

Product 1

HCID 66592352HCID 66592352, compoundYield 58.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Trityl chloride (9.43 g) is added in one portion to a solution of 2-hydroxymethyl-5-methoxy-4-pyridone (5 g) and 4-dimethylaminopyridine (4.2 g) in dry dimethylformamide (80 mL) and the solution stirred at room temperature for 12 hours. The mixture is then heated on a steam bath for 3 hours and diluted with iced water (300 mL) to give a light brown solid. The solid is collected, washed with water and sucked dry. The solid is dissolved in hot ethyl acetate to give a clear solution which immediately deposits a granular off-white solid. The solid does not redissolve on further heating. After cooling the solid is collected, washed with ethyl acetate and diethyl ether and dried to give 5-methoxy-2-trityloxymethyl-4-pyridone (7.5 g) as an off-white solid, m.p. 185-7° C.

Workup

  1. temperatureThe mixture is then heated on a steam bath for 3 hours
  2. customto give a light brown solid
  3. customThe solid is collected
  4. washwashed with water
  5. customsucked dry
  6. dissolutionThe solid is dissolved in hot ethyl acetate
  7. customto give a clear solution which
  8. dissolutionThe solid does not redissolve on further heating
  9. temperatureAfter cooling the solid
  10. customis collected
  11. washwashed with ethyl acetate and diethyl ether
  12. customdried

Sources & evidence

ORD record
ord-1b1eb50d34414e67b191977d96c37b90
Source dataset
uspto-grants-2010_01
Patent number
US07652144B2

Reaction notes

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